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Caught Mom with Best Friend (Trilogy)

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PART I Bedroom Fuck

The following is based on a true story…

My friend Ryan and I have been friends since high school. We would hang out at each other’s houses. We eventually graduated from high school and went to college. I stayed close to home by going to a local college. Ryan did the same thing. We would still hang out on a regular basis.

Ryan would be considered the ring leader of our group… the alpha male. He always got the ladies, while I was always pushed around and laughed at. Ryan always said, “Joe you have a smoking hot mom.” I didn’t want to say anything because I feared he might hit me or something. Ryan always had a thing for my mom (now in her 40s). She had a beautiful lean body, nice hair, and a good looking face. He would boldly flirt with her in front of me. She loved the attention Ryan gave her seeing that my dad divorced her two years ago. Ryan, now 21, was the ideal smooth talker. He can talk a lady into doing anything. As time progressed, I imagined what it would be like if Ryan fucked my mom. I jerked off to the idea several times. Yes, I am weird… so what? When I saw them together I started to get erections. Ryan continued making comments by calling my mom “a hot piece of ass” and “a MILF”. I continued to get turned on. He was so assertive and I was a little bitch that let him say whatever he wanted about my mom.

One night me and my four friends (including Ryan) came over to the house and chilled. We drank a couple of beers and smoked some pot in my basement. Mom stayed isolated in her part of the house most of the night. She only comes out when Ryan and I are alone. When others are over, she tends to be shy. As the night progressed, we watched movies and talked about girls. Ryan pressured me into drinking more beers. Before I knew it I was wasted. I was a lightweight. I started acting goofy. Ryan became annoyed with me and demanded for me to go to bed on the basement couch. I did what I was told. As I fell asl**p, my four friends (including Ryan) were just chilling watching a movie. I slept for about two or three hours before I woke up to a loud scream. It was around 2 am. I was still somewhat hammered. The TV was still on, but no one was around. I figured everyone had left (including Ryan).

The scream that woke me up…I didn’t hear it again. I must have dreamt it. My mouth was dry and I needed a cold glass of water. So I went upstairs to the kitchen. Once upstairs, I heard the screams again… they were coming from upstairs where my mom was supposedly sl**ping. The screams and moans were more consistent now. Instantly I thought someone was fucking my mom! My penis became slightly erect. I didn’t care anymore. I knew it was Ryan. A part of me wanted to see the action. I tiptoed upstairs in the dark. My mom’s door was closed. The moans were orgasmic now. I can hear the squeaking of the bedsprings in my mom’s bed. I slowly felt around for the doorknob. My dick was becoming harder. I discovered the doorknob and turned it slowly. Once the door was open, hot air hit me in the face. The vocals of my mom were no longer stifled by the closed door… they were as loud as ever. I looked inside my mom’s room… one little nightstand light was on. Most of the room was illuminated in a dim light. My eyes discovered my mom and Ryan. She was on top riding his dick. She was bouncing up and down. Her giant breasts were swaying back and forth… up and down. Sticky sweet covered both of their bodies. She began to cum like crazy all over Ryan. There was so much liquid. I placed my hand down my pants and began to stoke my dick though my boxers. My mom finally pulled off of Ryan revealing his massive cock. I retreated back into the darken hallway fearful that they might see me. Seconds later, I poked my head back into the room and found her sucking his massive cock. I never knew he was so well endowed. She began to suck his cock with such intensity. I finally felt vulnerable…like they might spot me. I also began to question myself, “Should I be here? This isn’t right. I should leave them alone to do their private business.” So I tiptoed back downstairs. I left the door partly ajar fearful they might hear me close it, because her loud moaning had stopped for that period of time. Back downstairs I felt an extreme wetness in my boxers. I ejaculated and didn’t even know it. I took my boxers off and fell back asl**p on the basement couch.

In the morning Ryan was gone. My mom was high on life. Both of them have no idea I saw them. I continue to ejaculate to what I saw that night. They still fuck around once in a while… but they tend to do it when I’m away from home. One day I drove home and discovered Ryan leaving my house with his clothes slightly messy. He lied to me by saying, “I came by to see if you were home… your mom let me in to wait.” But I know the truth. He was in there fucking her. He didn’t come to see me. He distracted me for a while and tried to keep me from going inside. Maybe my mom was still naked or something and Ryan didn’t want me to see.

PART II Leather Couch Fuck

The following is based on a true story…

My mom has been fucking my best friend (Ryan) for the past several months. My mom (who I haven’t named in my first story) is a nurse named Trish. She is a divorced mother of one (me) and she is in her early forties. She has a beautiful face, a good sized rack, and a lean body. Ryan is my age (in his early twenties). He works out a lot and is the ideal alpha male. All of the girls in high school and college desired him over me. One time I was kissing this girl and she called out Ryan’s name in an orgasmic way. My dick is weak… only 4 and a half inches hard. Ryan’s is a good 8 or 9 (based upon what I saw while he was plowing my mom).

Ryan and my mom have kept their relationship under wraps for the past several months. They have no clue that I know of them fucking around. Lately, their actions have been getting bolder. My mom is touching Ryan’s arms and shoulders more in public and she is constantly looking at him in a promiscuous way. However, I haven’t seen or heard them fuck since that night I spotted them in her bedroom.

I was becoming impatient. I came up with this plan that might allow for me to see them fuck again. I would tell her (my mom) that I was leaving for the rest of the day and night to stay over a friend’s house in Scranton. Before I left, I would leave the back door unlocked. Once I left, I would drive around or go somewhere and wait for mom to invite Ryan over. Once he came over and they were fucking, I would slip in through the back door, tip-toe upstairs, and either listen or watch them fuck.

As the school year came to a close, I told my mom one weekend that I wasn’t coming home that night because I was going to stay over at a friend’s house in Scranton. Her first question was: “Is Ryan going with you?” I replied, “No…He is not going.” I knew my plan was working. That afternoon, I jerked off in the bathroom to the image of my best friend filling my mom’s pussy with his cum. I got dressed in my good pair of jeans and put on one of my American Eagle shirts and told mom that I was leaving for the night. I climbed into my car and drove off to a local bar. My dick was hard the entire time. Even at the bar, I couldn’t get the image of Ryan and mom out of my head. I drank a little and chilled there for maybe three hours. I finally decided to drive by my house and see if Ryan’s car was parked within its proximity.

As I drove home, my balls were tingling and my dick was aching. Once I turned onto my street, I instantly saw Ryan’s black Mustang parked in my driveway. They’re fucking!!! I couldn’t wait to catch them in the act. I parked my car across the street from my house. I walked into the backyard. I could hear rap music blasting from inside my house. I knew Ryan loved rap. I slowly turned the door knob. Thankfully, my mom did not lock the backdoor while I was away! I carefully made my way into the house. I did not hear any moaning, just rap music. I then thought to myself, “What if they are NOT fucking?!! That would suck!!”

I turned the corner and was both shocked and excited by what I saw. My mom was bent over the living room couch while Ryan was fucking her from behind. My dick stood at attention. He stood there with his hands around my mom’s waist while he continued to plow her from behind. I could hear his balls slapping against my mom’s pussy (even with the rap music blasting). Her breasts were pushed up against the leather couch… so I didn’t get a good visual of them at first. I thought to myself: “This is even better than the first time.” The room was more illuminated… I could see everything. I boldly decided to stand there in the hallway. I don’t know why. Was it because I act more boldly when I drink? Possibly. I began to rub my little hard-on through my jeans. Maybe a minute or two later, Ryan pulled on my mom’s hair. Her breasts lifted off the coach and Ryan began to grope them [Lucky Bastard!!!]. She turned her head to either look back at Ryan or kiss him when she noticed me standing there in the hallway. I don’t know if she saw me feeling myself. All I know is she screamed and quickly tried to cover up her private parts with her hands. I think she even tried to grab some nearby clothes (but I can’t recall). Ryan pulled off of my mom and once again revealed his giant cock. I quickly realized I had an erection in my pants and hid behind the wall. Seconds later, I left the house, got into my car, and drove off. I eventually found a somewhat secluded area and jerked off in my pants. Now their relationship was out in the open.


The following is based on a true story…

After jerking off to the image of my friend fucking my mom, I decided to go back home and wash up. When I pulled up to the house, I realized Ryan’s black Mustang was no longer parked in the driveway. I opened the door… no one was around. I ran upstairs to take a shower and wash the sperm off me. After taking a long hot shower, I walked downstairs with the towel wrapped around my waist. I discovered mom sitting at the kitchen table. She looked distraught. The first thing she said to me was: “I’m sorry.” I stood there and really did not know what to say. My mom started talking again: “Ryan and I have been seeing one another for a while now [dating]… I’m so sorry… I know he’s your friend… I’m sorry… I’m sorry… I promise you this will never happen again.” I finally realized that I had to speak up and save their relationship for their sake and mine: “It’s okay mom… I’m okay with it. I understand it’s been a while since you’ve been with a man. I have no problem with you seeing Ryan… zero problem. I want to see you happy.” I then dropped a bombshell, “I know you two have been seeing one another. I’m totally cool with it.”

Mom sat speechless and then replied, “You knew?”

I responded, “I knew and I’m okay with it.” After further conversation, I finally left the kitchen and went upstairs. I wanted to leave her alone to think about what I had said. I texted Ryan and told him to “call me!!!” He never responded. Days turned into weeks without seeing or speaking to Ryan. Finally, I received a text from him inviting me to go out. He drove up to the house around 10 at night. He honked the horn and I left the house and got into his car. I had no idea where we were going. He drove dangerously fast down the street. The first words out of his mouth: “I know you know I’m seeing your mom. I saw her again last night.” I sat speechless. The balls this guy had to tell me this. He went on to say, “She came all over my backseat.” I sat there and began to get an erection… I laughed nervously at what he was saying. I had no idea if he was k**ding or not. He told me that he and she were “dating again.” He also informed me that I will be seeing more of him around the house. I nervously said, “Okay, alright.” He then drove me to a college party. He introduced me to everyone as the “son of that MILF I’m fucking.” I felt belittled.

The following day, mom broke the news to me that she and Ryan were “dating, but nothing more.” She wanted to know if I was okay with it. I told her that I was totally “cool” with it. She was so delighted to hear me say that. Her bight eyes expressed to me that she really liked him. I felt good. I was assisting with my mom’s wellbeing and happiness.

Trish, my mom, then informed me that she and Ryan were going out that night at 9:30. I watched as she got ready for him. She put on a tight red sweater, tight black leather pants, and high red heels. Her tits and ass looked so huge and perky. I never saw her dress so slutty in my life. A little after 9, Ryan pulled in the driveway and honked the horn. Mom gave me a big hug and a kiss on the cheek. She whispered in my ear, “Thank you.” If felt so good to see her happy again (especially after dad left). At the same time I had this strong sensual desire to see my alpha male friend fuck my sexy mom senselessly. I went in the bathroom and jerked off at least two times that night to the image of Ryan filling my mom’s pussy with his seed. After 3 am, I heard both of them come in. I pretended I was asl**p in my bed. I heard both of them talking and giggling. They both sounded d***k. Minutes later, I heard nothing but silence. They were most likely making out downstairs. An hour later, they both tip toed upstairs and closed my mom’s bedroom door. I heard the bed repeatedly squeak throughout the night. They were fucking only meters away!!! I couldn’t help but get out of bed, take off my boxers, and ejaculate in my beanbag chair in the corner of the room.

The next morning, I awoke and went downstairs only to see Ryan shirtless and in his underwear sitting on the living room couch. I couldn’t help but see his massive bulge. He had a big smile on his face and said, “Oh, look who just got up!” I giggled. I walked in the kitchen only to find my mom in a skimpy bathrobe; her tits were barely concealed. She asked me if I wanted any eggs. I responded “no thanks.” Ryan came in and put his hands on my shoulders. He then walked over to my mom and kissed her on the lips. She giggled while he looked right at me with a smirk. Later on that morning, I was sitting in the living room watching TV while mom was upstairs taking a shower in preparation for work. Ryan came over and sat right next to me in his underwear. He said, “Holy shit, your mom wore me out last night.” I just sat there watching TV and sarcastically responded with, “That’s great.” He replied, “I mean it. Your mom is one the best. Nice ass, amazing tits, tight body…” I then cut him off and said, “Okay, I get the picture.”

The following nights and mornings were the same. Ryan basically became a member of the f****y and stayed with us on a regular basis. One weekend I went out and returned home high on weed a little after 4 am. Ryan and mom were upstairs. The moaning and the orgasmic screams were so loud. I couldn’t help myself. I stripped off all of my clothes and sat on the leather living room sofa (where I found them fucking in the past) and began to wank in the dark to their lovemaking noises. Minutes later, there was silence. I did not know if they were done or not. I continued to jerk harder and harder. While I was wacking it, I did not hear Ryan come down the stairs. He turned the corner and turned the lights on. I was caught like a deer in the headlights. I was completely naked, my hand was on my hard cock, and my clothes were halfway across the room. I saw Ryan looking at me. He was completely naked. His dick appeared wet and semi-erect (still very large). He yelled and laughed at the same time, “What the fuck!? Put some clothes on you pervert!” I got up and ran over to my clothes on the floor. By the time I turned around, Ryan was headed back upstairs. I didn’t see Ryan for the rest of the night. He stayed with my mom in the bedroom. I went downstairs into the basement to fall asl**p.

The following morning, I walked upstairs and discovered Ryan at the kitchen table. My mom was upstairs taking a shower. Ryan laughed and jokingly yelled, “The pervert finally got up!” I nervously laughed at his joke. I went over to the refrigerator to get a drink of water. Ryan then said, “If you wanted to watch all you had to do was ask. Tonight I’ll leave the door open.” He continued to laugh. I had no idea if he was joking or not. I grabbed my water and headed into the living room.

That night, Ryan and mom went out on another date. They came home around 3:30ish. I pretended that I was asl**p like most previous nights. Both of them headed upstairs trying to keep their voices down. I listened intently. Minutes later, I heard the ever-so-common squeaking of my mom’s bed. I heard slight moaning. She tried to keep it down. I was curious; I wanted to see if he really left the door open. I haven’t seen them fucking in a while. I rolled out of bed without trying to make much noise. I tip-toed over to my door in the pitch blackness. While biting my lip, I slowly turned my doorknob. Once my door was open I saw some light peeking through the side of my mom’s bedroom door. Yes! The door was partly open! I tiptoed down the hallway to the entrance of my mom’s room. I looked through the crack. I had a hard time seeing anything. I slowed pushed the door a little more to see what was going on. Most of the room was illuminated in a dim light. I finally discovered what I was looking for. My mom was being fucked from behind by Ryan! My mom tried to stifle her moaning and screams by burrowing her face into a pillow; her hands gripped the pillow with such intensity. Her ass was up in the air. Ryan repeatedly plowed her from behind. I pulled out my dick and began to jerk it right there in the doorway. He looked over towards the door. I’m not sure if he saw me or not at the time, but he smiled and began to plow her even harder. I could hear his balls slapping my mom’s pussy. The bed began to squeak louder and louder. The volume of her moaning increased and she found it harder to keep it down. The fucking became so intense that the bed’s backboard began banging up against the wall. My mom began to yell into the pillow, “Oh my God! Oh my God! … I’m cumming!” I couldn’t take it anymore… I began to ejaculate all over the frame of the door. Ryan continued to fuck with a steady rhythm. Many minutes later, Ryan let out a loud grunt and began to cum inside my mom. I watched as he collapsed on top of my mom’s sweaty back. I tip toed back into my bedroom, where I cleaned myself off and climbed back into bed.

The next morning, Ryan was sitting on the living room couch watching TV. He asked me “Did you enjoy the show?” That‘s when I knew: He did see me last night! As the days progressed (and my mom was not around), he addressed me as a “fagot”, a “bitch” and a “weirdo.”

Updated: October 21, 2016 — 1:23 pm

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